Nitrogen → 2-Amino-5-(4-nitrophenyl)furan-3,4-dicarboxylic acid diethylester

HRID 1592932Notes

Reaction equation

HRID 1592932 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)Cl)[CH3:2].[CH2:19]([O:21][C:22](=[O:26])[CH2:23][C:24]#[N:25])[CH3:20].[Na].N#N>C1COCC1>[CH2:19]([O:21][C:22]([C:23]1[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:18])=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[O:17][C:24]=1[NH2:25])=[O:26])[CH3:20]

Participants

5

Reactant 3

HCID 947NitrogenHCID 135933914-Nitrobenzoyl-chloroacetic acid ethyl esterHCID 86596802HCID 86596802, compound

Product 1

HCID 694168472-Amino-5-(4-nitrophenyl)furan-3,4-dicarboxylic acid diethylester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

105 g (0.39 mols, 1 eq) of 4-nitrobenzoyl-chloroacetic acid ethyl ester are dissolved in 600 ml of THF. To this solution are added, on a water bath (T=35° C.), in portions, 49.4 g (0.37 mols) of finely ground sodium cyanoacetic acid ethyl ester (preparation: Chem, Ber. 1962, 95, 307-318.). It is stirred over night (under N2), fully concentrated by evaporation, and extracted with H2O and CH2Cl2. The combined CH2Cl2 phase is washed with H2O, and finally dried over MgSO4 and freed from solvent. Crystallisation from toluene yields the title compound, m.p.: 174-177° C.

Workup

  1. additionTo this solution are added, on a water bath (T=35° C.)
  2. concentrationfully concentrated by evaporation
  3. extractionextracted with H2O and CH2Cl2
  4. washThe combined CH2Cl2 phase is washed with H2O
  5. dry with materialfinally dried over MgSO4
  6. customCrystallisation from toluene

Sources & evidence

ORD record
ord-6f3993f5811b41b4ba112e8c77ef7f1d
Source dataset
uspto-grants-2007_11
Patent number
US07294633B2

Reaction notes

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